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Issue 24, 2002
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Nitroalkanes as nucleophiles in a self-catalytic Michael reaction

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Abstract

A simple, effective procedure for the preparation of 4-nitroalkanoates 6–9 by the Michael reaction of nitroalkanes 2–5 with the acrylate 1 is described. The primary nitro adduct 6 undergoes isomerization to hydroxamic acid 10 while heated in boiling nitromethane. Consecutive reactions of the latter compound lead to the formation of N-hydroxysuccinimide 11 and its N-ethoxy derivative 12. The spontaneous Nef reaction of the mother 4-nitrobutanoic acid 15 gives N-hydroxysuccinimide 14. The analogous reaction of secondary nitroalkanoic acids 16 and 17 provides 4-oxoalkanoic acids 18 and 19, respectively. Intramolecular participation by the carboxylic acid group in the Nef reaction is proposed.

Graphical abstract: Nitroalkanes as nucleophiles in a self-catalytic Michael reaction

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Publication details

The article was received on 23 Sep 2002, accepted on 15 Oct 2002 and first published on 13 Nov 2002


Article type: Paper
DOI: 10.1039/B209302M
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 2794-2798
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    Nitroalkanes as nucleophiles in a self-catalytic Michael reaction

    H. Krawczyk, W. M. Wolf and M. Śliwiński, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 2794
    DOI: 10.1039/B209302M

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